139165-12-1Relevant articles and documents
Enantioselective synthesis of the carbacephem antibiotic loracarbef via Mitsunobu and Dieckmann cyclization from an unnatural amino acid
Misner, Jerry W.,Fisher, Jack W.,Gardner, John P.,Pedersen, Steve W.,Trinkle, Kristina L.,Jackson, Billy G.,Zhang, Tony Y.
, p. 5991 - 5993 (2007/10/03)
The nucleus of the carbacephem antibiotic loracarbef was synthesized in a highly efficient and enantioselective fashion from 2S,3S-2-amino-3-hydroxy-6-heptenoic acid (AHHA), which was derived from enzyme-catalyzed condensation of glycine and 4-pentenaldehyde. The bicyclic framework of this compound was established through sequential Mitsunobu reaction and aldol condensations.
Scope of phthalimido chemistry I. Extension of utility by conversion to the opcb protecting group
Astleford, Bret,Weigel, Leland O.
, p. 3301 - 3304 (2007/10/02)
The scope of the phthalimido protecting group (PhthN-) is extended by reaction with pyrrolidine. The resulting o-pyrrolidinocarbonylbenzamide ("OPCB-") represents a base/nucleophile stable derivative of the parent, which reverts to the imide form upon treatment with acid. This methodology allows utilization of this protecting group (as the OPCB form in synthetic sequences requiring basic/nucleophilic reaction conditions.